IL131713A - Dosage forms comprising separate portions of r- and s-enantiomers - Google Patents
Dosage forms comprising separate portions of r- and s-enantiomersInfo
- Publication number
- IL131713A IL131713A IL13171398A IL13171398A IL131713A IL 131713 A IL131713 A IL 131713A IL 13171398 A IL13171398 A IL 13171398A IL 13171398 A IL13171398 A IL 13171398A IL 131713 A IL131713 A IL 131713A
- Authority
- IL
- Israel
- Prior art keywords
- enantiomer
- dosage form
- form according
- enantiomers
- different
- Prior art date
Links
- 239000002552 dosage form Substances 0.000 title claims abstract description 73
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims abstract description 66
- 229940079593 drug Drugs 0.000 claims abstract description 43
- 239000003814 drug Substances 0.000 claims abstract description 43
- SGTNSNPWRIOYBX-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC=C(OC)C(OC)=C1 SGTNSNPWRIOYBX-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229960001722 verapamil Drugs 0.000 claims abstract description 5
- 239000003826 tablet Substances 0.000 claims description 26
- TVYLLZQTGLZFBW-ZBFHGGJFSA-N (R,R)-tramadol Chemical compound COC1=CC=CC([C@]2(O)[C@H](CCCC2)CN(C)C)=C1 TVYLLZQTGLZFBW-ZBFHGGJFSA-N 0.000 claims description 18
- TVYLLZQTGLZFBW-GOEBONIOSA-N tramadol Natural products COC1=CC=CC([C@@]2(O)[C@@H](CCCC2)CN(C)C)=C1 TVYLLZQTGLZFBW-GOEBONIOSA-N 0.000 claims description 17
- 230000000694 effects Effects 0.000 claims description 14
- 229960004380 tramadol Drugs 0.000 claims description 12
- 239000007943 implant Substances 0.000 claims description 10
- PJVWKTKQMONHTI-UHFFFAOYSA-N warfarin Chemical compound OC=1C2=CC=CC=C2OC(=O)C=1C(CC(=O)C)C1=CC=CC=C1 PJVWKTKQMONHTI-UHFFFAOYSA-N 0.000 claims description 8
- 229960005080 warfarin Drugs 0.000 claims description 8
- 239000012729 immediate-release (IR) formulation Substances 0.000 claims description 7
- 239000000443 aerosol Substances 0.000 claims description 6
- 239000007942 layered tablet Substances 0.000 claims description 6
- 239000011859 microparticle Substances 0.000 claims description 6
- 230000002411 adverse Effects 0.000 claims description 4
- 239000002775 capsule Substances 0.000 claims description 4
- 230000003204 osmotic effect Effects 0.000 claims description 4
- 229920000642 polymer Polymers 0.000 claims description 4
- 238000005086 pumping Methods 0.000 claims description 4
- 230000009471 action Effects 0.000 claims description 3
- 230000007423 decrease Effects 0.000 claims description 3
- VLPIATFUUWWMKC-SNVBAGLBSA-N (2r)-1-(2,6-dimethylphenoxy)propan-2-amine Chemical compound C[C@@H](N)COC1=C(C)C=CC=C1C VLPIATFUUWWMKC-SNVBAGLBSA-N 0.000 claims description 2
- AGBQKNBQESQNJD-SSDOTTSWSA-N (R)-lipoic acid Chemical compound OC(=O)CCCC[C@@H]1CCSS1 AGBQKNBQESQNJD-SSDOTTSWSA-N 0.000 claims description 2
- SGUAFYQXFOLMHL-UHFFFAOYSA-N 2-hydroxy-5-{1-hydroxy-2-[(4-phenylbutan-2-yl)amino]ethyl}benzamide Chemical compound C=1C=C(O)C(C(N)=O)=CC=1C(O)CNC(C)CCC1=CC=CC=C1 SGUAFYQXFOLMHL-UHFFFAOYSA-N 0.000 claims description 2
- FEROPKNOYKURCJ-UHFFFAOYSA-N 4-amino-N-(1-azabicyclo[2.2.2]octan-3-yl)-5-chloro-2-methoxybenzamide Chemical compound COC1=CC(N)=C(Cl)C=C1C(=O)NC1C(CC2)CCN2C1 FEROPKNOYKURCJ-UHFFFAOYSA-N 0.000 claims description 2
- JOATXPAWOHTVSZ-UHFFFAOYSA-N Celiprolol Chemical compound CCN(CC)C(=O)NC1=CC=C(OCC(O)CNC(C)(C)C)C(C(C)=O)=C1 JOATXPAWOHTVSZ-UHFFFAOYSA-N 0.000 claims description 2
- JRWZLRBJNMZMFE-UHFFFAOYSA-N Dobutamine Chemical compound C=1C=C(O)C(O)=CC=1CCNC(C)CCC1=CC=C(O)C=C1 JRWZLRBJNMZMFE-UHFFFAOYSA-N 0.000 claims description 2
- DJBNUMBKLMJRSA-UHFFFAOYSA-N Flecainide Chemical compound FC(F)(F)COC1=CC=C(OCC(F)(F)F)C(C(=O)NCC2NCCCC2)=C1 DJBNUMBKLMJRSA-UHFFFAOYSA-N 0.000 claims description 2
- UEQUQVLFIPOEMF-UHFFFAOYSA-N Mianserin Chemical compound C1C2=CC=CC=C2N2CCN(C)CC2C2=CC=CC=C21 UEQUQVLFIPOEMF-UHFFFAOYSA-N 0.000 claims description 2
- IUJDSEJGGMCXSG-UHFFFAOYSA-N Thiopental Chemical compound CCCC(C)C1(CC)C(=O)NC(=S)NC1=O IUJDSEJGGMCXSG-UHFFFAOYSA-N 0.000 claims description 2
- 229960004607 alfuzosin Drugs 0.000 claims description 2
- WNMJYKCGWZFFKR-UHFFFAOYSA-N alfuzosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(C)CCCNC(=O)C1CCCO1 WNMJYKCGWZFFKR-UHFFFAOYSA-N 0.000 claims description 2
- AGBQKNBQESQNJD-UHFFFAOYSA-N alpha-Lipoic acid Natural products OC(=O)CCCCC1CCSS1 AGBQKNBQESQNJD-UHFFFAOYSA-N 0.000 claims description 2
- ROBVIMPUHSLWNV-UHFFFAOYSA-N aminoglutethimide Chemical compound C=1C=C(N)C=CC=1C1(CC)CCC(=O)NC1=O ROBVIMPUHSLWNV-UHFFFAOYSA-N 0.000 claims description 2
- 229960003437 aminoglutethimide Drugs 0.000 claims description 2
- 229960004195 carvedilol Drugs 0.000 claims description 2
- NPAKNKYSJIDKMW-UHFFFAOYSA-N carvedilol Chemical compound COC1=CC=CC=C1OCCNCC(O)COC1=CC=CC2=NC3=CC=C[CH]C3=C12 NPAKNKYSJIDKMW-UHFFFAOYSA-N 0.000 claims description 2
- 229960002320 celiprolol Drugs 0.000 claims description 2
- 229960005132 cisapride Drugs 0.000 claims description 2
- DCSUBABJRXZOMT-IRLDBZIGSA-N cisapride Chemical compound C([C@@H]([C@@H](CC1)NC(=O)C=2C(=CC(N)=C(Cl)C=2)OC)OC)N1CCCOC1=CC=C(F)C=C1 DCSUBABJRXZOMT-IRLDBZIGSA-N 0.000 claims description 2
- DCSUBABJRXZOMT-UHFFFAOYSA-N cisapride Natural products C1CC(NC(=O)C=2C(=CC(N)=C(Cl)C=2)OC)C(OC)CN1CCCOC1=CC=C(F)C=C1 DCSUBABJRXZOMT-UHFFFAOYSA-N 0.000 claims description 2
- UVTNFZQICZKOEM-UHFFFAOYSA-N disopyramide Chemical compound C=1C=CC=NC=1C(C(N)=O)(CCN(C(C)C)C(C)C)C1=CC=CC=C1 UVTNFZQICZKOEM-UHFFFAOYSA-N 0.000 claims description 2
- 229960001066 disopyramide Drugs 0.000 claims description 2
- 229960001089 dobutamine Drugs 0.000 claims description 2
- 229960000449 flecainide Drugs 0.000 claims description 2
- XXSMGPRMXLTPCZ-UHFFFAOYSA-N hydroxychloroquine Chemical compound ClC1=CC=C2C(NC(C)CCCN(CCO)CC)=CC=NC2=C1 XXSMGPRMXLTPCZ-UHFFFAOYSA-N 0.000 claims description 2
- 229960004171 hydroxychloroquine Drugs 0.000 claims description 2
- HOMGKSMUEGBAAB-UHFFFAOYSA-N ifosfamide Chemical compound ClCCNP1(=O)OCCCN1CCCl HOMGKSMUEGBAAB-UHFFFAOYSA-N 0.000 claims description 2
- 229960001101 ifosfamide Drugs 0.000 claims description 2
- 235000019136 lipoic acid Nutrition 0.000 claims description 2
- 229960003404 mexiletine Drugs 0.000 claims description 2
- 229960003955 mianserin Drugs 0.000 claims description 2
- JWHAUXFOSRPERK-UHFFFAOYSA-N propafenone Chemical compound CCCNCC(O)COC1=CC=CC=C1C(=O)CCC1=CC=CC=C1 JWHAUXFOSRPERK-UHFFFAOYSA-N 0.000 claims description 2
- 229960000203 propafenone Drugs 0.000 claims description 2
- WFWLQNSHRPWKFK-ZCFIWIBFSA-N tegafur Chemical compound O=C1NC(=O)C(F)=CN1[C@@H]1OCCC1 WFWLQNSHRPWKFK-ZCFIWIBFSA-N 0.000 claims description 2
- 229960001674 tegafur Drugs 0.000 claims description 2
- VCKUSRYTPJJLNI-UHFFFAOYSA-N terazosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1CCCO1 VCKUSRYTPJJLNI-UHFFFAOYSA-N 0.000 claims description 2
- 229960001693 terazosin Drugs 0.000 claims description 2
- 229960002663 thioctic acid Drugs 0.000 claims description 2
- 229960003279 thiopental Drugs 0.000 claims description 2
- 230000001988 toxicity Effects 0.000 claims description 2
- 231100000419 toxicity Toxicity 0.000 claims description 2
- 229950004681 zacopride Drugs 0.000 claims description 2
- 239000002245 particle Substances 0.000 claims 3
- -1 citalopra Chemical compound 0.000 claims 2
- 239000012730 sustained-release form Substances 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000013270 controlled release Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- PPKXEPBICJTCRU-XMZRARIVSA-N (R,R)-tramadol hydrochloride Chemical compound Cl.COC1=CC=CC([C@]2(O)[C@H](CCCC2)CN(C)C)=C1 PPKXEPBICJTCRU-XMZRARIVSA-N 0.000 description 5
- PPKXEPBICJTCRU-KUARMEPBSA-N (S,S)-tramadol hydrochloride Chemical compound Cl.COC1=CC=CC([C@@]2(O)[C@@H](CCCC2)CN(C)C)=C1 PPKXEPBICJTCRU-KUARMEPBSA-N 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 230000036592 analgesia Effects 0.000 description 3
- 230000000202 analgesic effect Effects 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 239000012738 dissolution medium Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 3
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 3
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 3
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 230000002459 sustained effect Effects 0.000 description 3
- PJVWKTKQMONHTI-HNNXBMFYSA-N (S)-warfarin Chemical compound C1([C@H](CC(=O)C)C=2C(OC3=CC=CC=C3C=2O)=O)=CC=CC=C1 PJVWKTKQMONHTI-HNNXBMFYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 238000009115 maintenance therapy Methods 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 150000003839 salts Chemical group 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WSEQXVZVJXJVFP-HXUWFJFHSA-N (R)-citalopram Chemical compound C1([C@@]2(C3=CC=C(C=C3CO2)C#N)CCCN(C)C)=CC=C(F)C=C1 WSEQXVZVJXJVFP-HXUWFJFHSA-N 0.000 description 1
- 102000009027 Albumins Human genes 0.000 description 1
- 108010088751 Albumins Proteins 0.000 description 1
- 229920002785 Croscarmellose sodium Polymers 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 208000032843 Hemorrhage Diseases 0.000 description 1
- 206010028813 Nausea Diseases 0.000 description 1
- 102000003840 Opioid Receptors Human genes 0.000 description 1
- 108090000137 Opioid Receptors Proteins 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000002429 anti-coagulating effect Effects 0.000 description 1
- 230000003502 anti-nociceptive effect Effects 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 229940127219 anticoagulant drug Drugs 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000004296 chiral HPLC Methods 0.000 description 1
- 229960001653 citalopram Drugs 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229960001681 croscarmellose sodium Drugs 0.000 description 1
- 235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 208000002173 dizziness Diseases 0.000 description 1
- 238000009510 drug design Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000003628 erosive effect Effects 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- TVURRHSHRRELCG-UHFFFAOYSA-N fenoldopam Chemical compound C1=CC(O)=CC=C1C1C2=CC(O)=C(O)C(Cl)=C2CCNC1 TVURRHSHRRELCG-UHFFFAOYSA-N 0.000 description 1
- 229960002724 fenoldopam Drugs 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 238000009478 high shear granulation Methods 0.000 description 1
- 230000002299 hypoprothrombinemic effect Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- 230000000966 norepinephrine reuptake Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 230000036407 pain Effects 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000036515 potency Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000000697 serotonin reuptake Effects 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 229960003107 tramadol hydrochloride Drugs 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2072—Pills, tablets, discs, rods characterised by shape, structure or size; Tablets with holes, special break lines or identification marks; Partially coated tablets; Disintegrating flat shaped forms
- A61K9/2086—Layered tablets, e.g. bilayer tablets; Tablets of the type inert core-active coat
- A61K9/209—Layered tablets, e.g. bilayer tablets; Tablets of the type inert core-active coat containing drug in at least two layers or in the core and in at least one outer layer
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
- A61K9/2054—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
Landscapes
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9704978.7A GB9704978D0 (en) | 1997-03-11 | 1997-03-11 | Dosage forms |
| GBGB9719261.1A GB9719261D0 (en) | 1997-09-10 | 1997-09-10 | Dosage forms |
| PCT/GB1998/000726 WO1998040053A1 (en) | 1997-03-11 | 1998-03-11 | Dosage forms comprising separate portions of r- and s-enantiomers |
| US09/038,873 US6056968A (en) | 1997-03-11 | 1998-03-11 | Pharmaceutical drug dosage forms providing different release rates |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL131713A0 IL131713A0 (en) | 2001-03-19 |
| IL131713A true IL131713A (en) | 2004-08-31 |
Family
ID=27268767
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL13171398A IL131713A (en) | 1997-03-11 | 1998-03-11 | Dosage forms comprising separate portions of r- and s-enantiomers |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US6056968A (https=) |
| EP (1) | EP0969818B1 (https=) |
| JP (1) | JP2001514651A (https=) |
| CN (1) | CN1251987A (https=) |
| AT (1) | ATE275394T1 (https=) |
| AU (1) | AU741821B2 (https=) |
| BR (1) | BR9808325A (https=) |
| CA (1) | CA2285407C (https=) |
| DE (1) | DE69826113T2 (https=) |
| ES (1) | ES2227814T3 (https=) |
| HU (1) | HUP0000759A3 (https=) |
| IL (1) | IL131713A (https=) |
| NO (1) | NO994412L (https=) |
| PL (1) | PL335619A1 (https=) |
| WO (1) | WO1998040053A1 (https=) |
Families Citing this family (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5912268A (en) * | 1995-05-22 | 1999-06-15 | Alza Corporation | Dosage form and method for treating incontinence |
| US6262115B1 (en) * | 1995-05-22 | 2001-07-17 | Alza Coporation | Method for the management of incontinence |
| HUP0104420A2 (en) * | 1998-12-02 | 2002-08-28 | Darwin Discovery Ltd | Therapeutic composition containing a new form of tramadol and its use |
| AU3064800A (en) * | 1999-01-21 | 2000-08-07 | Darwin Discovery Limited | The therapeutic use of r-warfarin as anticoagulant |
| US20030170181A1 (en) * | 1999-04-06 | 2003-09-11 | Midha Kamal K. | Method for preventing abuse of methylphenidate |
| PE20010623A1 (es) * | 1999-10-05 | 2001-07-07 | Gruenenthal Chemie | Uso de (+)-tramadol y/o o-demetiltramadol para tratamiento de urgencia urinaria incrementada y/o incontinencia urinaria |
| EP1313460A2 (en) * | 1999-11-09 | 2003-05-28 | Darwin Discovery Limited | Therapeutic use and formulation of (-)-tramadol |
| DE10004926A1 (de) | 2000-02-04 | 2001-08-09 | Gruenenthal Gmbh | Verfahren zur enzymatischen Racematspaltung von Aminomethyl-Aryl-Cyclohexanol-Derivaten |
| AU3582101A (en) | 2000-03-01 | 2001-09-12 | Euro-Celtique S.A. | The treatment of functional gastrointestinal disorders |
| US20010036959A1 (en) * | 2000-04-03 | 2001-11-01 | Gabel Rolf Dieter | Carvedilol-hydrophilic solutions |
| CA2423558A1 (en) * | 2000-10-03 | 2002-04-11 | Penwest Pharmaceuticals Company | Delivery system for multi-pharmaceutical active materials at various release rates |
| WO2002065834A2 (en) * | 2000-10-24 | 2002-08-29 | Smithkline Beecham Corporation | Novel formulations of carvedilol |
| US6562871B1 (en) * | 2000-11-06 | 2003-05-13 | Boehringer Ingelheim Pharmaceuticals, Inc. | Dry granulation of pharmaceutical formulation comprising mexiletine |
| DE10108122A1 (de) * | 2001-02-21 | 2002-10-02 | Gruenenthal Gmbh | Arzneimittel auf Basis von Tramadol |
| IN191028B (https=) * | 2001-05-17 | 2003-09-13 | Sun Pharmaceutical Ind Ltd | |
| US8101209B2 (en) * | 2001-10-09 | 2012-01-24 | Flamel Technologies | Microparticulate oral galenical form for the delayed and controlled release of pharmaceutical active principles |
| WO2003048113A1 (en) | 2001-11-30 | 2003-06-12 | Sepracor Inc. | Tramadol analogs and uses thereof |
| US8128957B1 (en) | 2002-02-21 | 2012-03-06 | Valeant International (Barbados) Srl | Modified release compositions of at least one form of tramadol |
| US20050182056A9 (en) * | 2002-02-21 | 2005-08-18 | Seth Pawan | Modified release formulations of at least one form of tramadol |
| EP1562552A1 (en) * | 2002-11-08 | 2005-08-17 | Egalet A/S | Controlled release carvedilol compositions |
| WO2004056336A2 (en) * | 2002-12-20 | 2004-07-08 | Ranbaxy Laboratories Limited | Controlled release, multiple unit drug delivery systems |
| WO2004071501A1 (en) * | 2003-02-10 | 2004-08-26 | Shire Biochem Inc. | Enantiomeric amphetamine compositions for the treatment of adhd |
| WO2004103361A2 (en) * | 2003-05-20 | 2004-12-02 | Ranbaxy Laboratories Limited | A pharmaceutical dosage form of citalopram |
| US8263126B2 (en) * | 2003-06-06 | 2012-09-11 | Ethypharm | Orally-dispersible multilayer tablet |
| US20060172006A1 (en) * | 2003-10-10 | 2006-08-03 | Vincent Lenaerts | Sustained-release tramadol formulations with 24-hour clinical efficacy |
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| EP1686967A4 (en) * | 2003-11-25 | 2012-08-08 | Smithkline Beecham Cork Ltd | CARVEDILOL-FREE BASE, SALTS, WATER-FREE FORMS OR SOLVATES THEREOF, CORRESPONDING PHARMACEUTICAL COMPOSITIONS, CONTROLLED RELEASE FORMULAS AND TREATMENT OR DISPOSAL PROCEDURES |
| AU2005284908B2 (en) | 2004-09-13 | 2011-12-08 | Morningside Venture Investments Limited | Biosynchronous transdermal drug delivery |
| AU2005290829B2 (en) * | 2004-10-01 | 2011-06-09 | Nippon Zoki Pharmaceutical Co., Ltd. | Solid pharmaceutical preparation |
| WO2007048219A2 (en) | 2005-09-09 | 2007-05-03 | Labopharm Inc. | Sustained drug release composition |
| EP1976488A4 (en) * | 2006-01-12 | 2010-02-10 | Wockhardt Ltd | ALFUZOSIN PROLONGED RELEASE PREPARATIONS |
| JP5120652B2 (ja) * | 2006-03-30 | 2013-01-16 | 日本臓器製薬株式会社 | 固形医薬製剤 |
| CN101674728A (zh) | 2007-02-12 | 2010-03-17 | Dmi生物科学公司 | 降低曲马多的副作用 |
| CA2677690C (en) * | 2007-02-12 | 2012-05-15 | James V. Winkler | Treatment of comorbid premature ejaculation and erectile dysfunction |
| CN103977003A (zh) | 2007-04-02 | 2014-08-13 | 帕金森氏病研究院 | 用于降低治疗的副作用的方法和组合物 |
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|---|---|---|---|---|
| US4818541A (en) * | 1987-08-19 | 1989-04-04 | Schering Corporation | Transdermal delivery of enantiomers of phenylpropanolamine |
| US5145866A (en) * | 1991-04-22 | 1992-09-08 | Hoechst-Roussel Pharmaceuticals Incorporated | Method of treating anxiety with the aid of r(+)-3-amino-1-hydroxy-pyrrolidin-2-one |
| US5204116A (en) * | 1991-05-01 | 1993-04-20 | Alza Corporation | Dosage form providing immediate therapy followed by prolonged therapy |
| NZ260408A (en) * | 1993-05-10 | 1996-05-28 | Euro Celtique Sa | Controlled release preparation comprising tramadol |
| DE4319438C1 (de) * | 1993-06-11 | 1994-06-01 | Gerd Dr Dr Geislinger | Arzneimittel auf der Grundlage von Ketoprofen zur Bekämpfung von Schmerzen und/oder Entzündungen und/oder Fieber an Menschen und Tieren |
| GB9412689D0 (en) * | 1994-06-23 | 1994-08-10 | Chiroscience Ltd | Cytotoxic agent and its use |
-
1998
- 1998-03-11 IL IL13171398A patent/IL131713A/en not_active IP Right Cessation
- 1998-03-11 EP EP98910863A patent/EP0969818B1/en not_active Expired - Lifetime
- 1998-03-11 AU AU65089/98A patent/AU741821B2/en not_active Ceased
- 1998-03-11 JP JP53935798A patent/JP2001514651A/ja not_active Ceased
- 1998-03-11 ES ES98910863T patent/ES2227814T3/es not_active Expired - Lifetime
- 1998-03-11 PL PL98335619A patent/PL335619A1/xx unknown
- 1998-03-11 HU HU0000759A patent/HUP0000759A3/hu unknown
- 1998-03-11 DE DE69826113T patent/DE69826113T2/de not_active Expired - Fee Related
- 1998-03-11 CN CN98804125.1A patent/CN1251987A/zh active Pending
- 1998-03-11 CA CA002285407A patent/CA2285407C/en not_active Expired - Fee Related
- 1998-03-11 US US09/038,873 patent/US6056968A/en not_active Expired - Fee Related
- 1998-03-11 AT AT98910863T patent/ATE275394T1/de not_active IP Right Cessation
- 1998-03-11 BR BR9808325-2A patent/BR9808325A/pt not_active IP Right Cessation
- 1998-03-11 WO PCT/GB1998/000726 patent/WO1998040053A1/en not_active Ceased
-
1999
- 1999-09-10 NO NO994412A patent/NO994412L/no not_active Application Discontinuation
-
2000
- 2000-01-05 US US09/478,177 patent/US6221394B1/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| NO994412D0 (no) | 1999-09-10 |
| BR9808325A (pt) | 2000-05-16 |
| US6221394B1 (en) | 2001-04-24 |
| AU6508998A (en) | 1998-09-29 |
| IL131713A0 (en) | 2001-03-19 |
| AU741821B2 (en) | 2001-12-13 |
| NO994412L (no) | 1999-10-20 |
| CN1251987A (zh) | 2000-05-03 |
| DE69826113T2 (de) | 2005-01-20 |
| PL335619A1 (en) | 2000-05-08 |
| US6056968A (en) | 2000-05-02 |
| ATE275394T1 (de) | 2004-09-15 |
| ES2227814T3 (es) | 2005-04-01 |
| HUP0000759A3 (en) | 2000-11-28 |
| HUP0000759A2 (hu) | 2000-10-28 |
| EP0969818A1 (en) | 2000-01-12 |
| DE69826113D1 (de) | 2004-10-14 |
| CA2285407A1 (en) | 1998-09-17 |
| CA2285407C (en) | 2006-08-01 |
| WO1998040053A1 (en) | 1998-09-17 |
| EP0969818B1 (en) | 2004-09-08 |
| JP2001514651A (ja) | 2001-09-11 |
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| FF | Patent granted | ||
| MM9K | Patent not in force due to non-payment of renewal fees |